Ethanol → HCID 68604460, compound

HRID 1848600Notes

Reaction equation

HRID 1848600 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]([CH3:22])[C:9]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:10]=2[O:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:7])=[CH:4][C:3]=1[C:25]1[CH:26]=[N:27][C:28]([C:32]#[N:33])=[CH:29][C:30]=1[CH3:31].[C:34](Cl)(=O)[C:35](Cl)=O.C(O)C>C(Cl)Cl.CN(C=O)C>[CH2:34]([O:15][C:14](=[O:16])[CH2:13][CH2:12][O:11][C:10]1[C:17]([CH3:21])=[CH:18][CH:19]=[CH:20][C:9]=1[N:8]([C:6](=[O:7])[C:5]1[CH:23]=[CH:24][C:2]([Cl:1])=[C:3]([C:25]2[CH:26]=[N:27][C:28]([C:32]#[N:33])=[CH:29][C:30]=2[CH3:31])[CH:4]=1)[CH3:22])[CH3:35]

Participants

6

Reactant 3

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 68602821HCID 68602821, compound

Product 1

HCID 68604460HCID 68604460, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-{[4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-6-methyl-phenoxy)-propionic acid (160 mg, 0.35 mmol) in DCM (15 mL) was added oxalyl chloride (45.2 μL, 0.52 mmol) and 1 drop of DMF. The solution was stirred for 30 minutes before addition of ethanol (5 mL). The solution was stirred for a further 30 minutes at which time the solvent was evaporated and the residue purified by preparative TLC [eluent: 50% ethyl acetate in hexane] to yield 3-(2-{[4-chloro-3-(6-cyano-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-6-methyl-phenoxy)-propionic acid ethyl ester 16-1 (125 mg). MS [M+H]+: 492.4; tR=5.45 min. (method 4).

Workup

  1. customwas evaporated
  2. customthe residue purified by preparative TLC [eluent: 50% ethyl acetate in hexane]

Sources & evidence

ORD record
ord-6014f052a4554736be25fe68351055c2
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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